My history is surprisingly similar to yours, I started in 1999, I used Notepad as my first text editor, and by 2003 I got caught up in the movement towards making markup strict, which I felt was the mark of professionalism. However, by 2006 I had mostly rejected the notion of “strictness”. There were several things that turned me against strictness. One of them was Mark Pilgrim’s essay “XML on the Web Has Failed”:

https://www.xml.com/pub/a/2004/07/21/dive.html

Another problem was brought up by Sam Ruby: his daughter sent him an image, which he wanted to share on MySpace, but he couldn’t. And the reason he couldn’t was because the image was in a SVG format which required strict XML, and MySpace was, of course, very far from anything “strict”.

Some people looked at the chaos of non-standard HTML and decided the Web was successful because it had been broken from the beginning, and it had learned to work well while broken. I reached a different conclusion. It became clear to me that what developers wanted to do simply had nothing to do with HTTP/HTML.

We don’t yet have the technology to do what developers want to do. HTML was an interesting experiment, but it suffered from a dual mandate. Sir Tim Berners Lee wanted HTML to both structure data and also present it in graphical form. Almost from the start, developers were conflicted about which mandate they should obey, but the preference, since at least 1993, if not earlier, was to give priority to the visual. For all practical purposes, developers saw HTTP/HTML as GUI for IP/TCP. Previous IP/TCP technologies (email, gopher, ftp) had lacked a visual component, but HTML finally offered a standard way to send things over Internet and format the end result visually (emphasis on “standard”; I could insert an aside here about X window systems and some cool software of that era, but every app implemented their own ideas about visual presentation. X-Emacs, for instance, had its own system for visual formatting over a network).

That we now have so many versions of languages that compile back to Javascript, which renders HTML, shows that there is a great hunger for something that moves beyond HTTP/HTML.

The quote that Mark Pilgrim used at the beginning of his article is worth repeating:

“There must have been a moment, at the beginning, where we could have said … no. Somehow we missed it. Well, we’ll know better next time.”

“Until then …”

– Rosencrantz and Guildenstern are Dead

He may have meant that ironically (since Rosencrantz and Guildenstern are murdered) but I like to think that we will eventually get rid of HTTP/HTML and replace it with what developers actually want: a pure GUI for IP/TCP, a technology with a single mandate, with no burden of also offering semantics or structure or hierarchy.